methyl N-benzyl-P-phenylphosphonamidate | 1262801-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-benzyl-P-phenylphosphonamidate
• CAS: 1262801-00-2
• 化学式: C₁₄H₁₆NO₂P
• 分子量: 261.26
• InChiKey: VSRIZIUYEJFGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 牛血清白蛋白 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 2.5h， 生成 methyl N-benzyl-P-phenylphosphonamidate
  参考文献：
  名称：

  通过甲硅烷基次膦酸和酯的斯托丁格反应合成膦酰胺肽。

  摘要：

  未保护的叠氮基肽与甲硅烷基次膦酸和固相支持物上的酯的Staudinger反应可在温和的条件下以高纯度和高收率直接无酸地进入不同的膦酰胺酸肽酯或酸。

  DOI：

  10.1039/c0cc02472d

文献信息

• Cobalt-catalyzed oxidative arylmethylation of phosphorylamides
  作者：Jing Xiao、Ping Li、Yingjun Zhang、Dexun Xie、Zhihong Peng、Delie An、Wanrong Dong

  DOI：10.1016/j.tet.2018.07.006

  日期：2018.8

  A cobalt-catalyzed strategy for N-arylmethylation of phosphorylamides was herein achieved with the assistance of azodiisobutyronitrile as the radical initiator and di-tert-butyl peroxide as the oxidant. Both methylarenes and diaryl methanes were compatible under the oxidative conditions, expressing broad substrate scope (51 examples) and high efficiency (up to 87% yield).

  对于A钴催化的策略Ñ phosphorylamides的-arylmethylation被本文偶氮二异丁腈的协助下作为自由基引发剂和二-实现叔丁基过氧化物作为氧化剂。甲基芳烃和二芳基甲烷在氧化条件下均相容，表现出广泛的底物范围（51个实例）和高效率（产率高达87％）。
• Copper-Catalyzed (Di)Arylmethylation of Phosphorylamides Under Oxidative Conditions
  作者：Zijian Zhao、Xiaobo Liu、Anguo Hou、Yan Lian

  DOI：10.1002/ejoc.201801194

  日期：2018.12.31

  A CuI‐catalyzed phosphorylamidation of benzylic C–H bonds was demonstrated. Both methylarenes and diaryl methanes were compatible in the system with broad functional groups tolerance and good efficiency (51 examples, up to 92 % yields).

  证明了Cu I催化的苄基CH键的磷酸化作用。甲基芳烃和二芳基甲烷在系统中均兼容，具有宽泛的官能团耐受性和良好的效率（51个实例，收率高达92％）。
• Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins
  作者：M. Robert J. Vallée、Paul Majkut、Ina Wilkening、Christoph Weise、Gregor Müller、Christian P. R. Hackenberger

  DOI：10.1021/ol2020175

  日期：2011.10.21

  Site-specific functionalization of proteins by bloorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with ollgoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.